Amarogentin

Amarogentin
	; Chemical structure of amarogentin
Names
	IUPAC name [(2S,3R,4S,5S,6R)-2-[[(3S,4R,4aS)-4-Ethenyl-8-oxo-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-3-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]2,4-dihydroxy-6-(3-hydroxyphenyl)benzoate
Identifiers
CAS Number	21018-84-8 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:2622 ;
ChEMBL	ChEMBL451112 ;
ChemSpider	103033 ;
PubChem CID	115149;
UNII	5L82GT5I0W ;
	InChI InChI=1S/C29H30O13/c1-2-16-17-6-7-38-26(36)19(17)12-39-28(16)42-29-25(24(35)23(34)21(11-30)40-29)41-27(37)22-18(9-15(32)10-20(22)33)13-4-3-5-14(31)8-13/h2-5,8-10,12,16-17,21,23-25,28-35H,1,6-7,11H2/t16-,17+,21-,23-,24+,25-,28+,29+/m1/s1 Key: DBOVHQOUSDWAPQ-WTONXPSSSA-N ; InChI=1/C29H30O13/c1-2-16-17-6-7-38-26(36)19(17)12-39-28(16)42-29-25(24(35)23(34)21(11-30)40-29)41-27(37)22-18(9-15(32)10-20(22)33)13-4-3-5-14(31)8-13/h2-5,8-10,12,16-17,21,23-25,28-35H,1,6-7,11H2/t16-,17+,21-,23-,24+,25-,28+,29+/m1/s1 Key: DBOVHQOUSDWAPQ-WTONXPSSBG;
	SMILES O=C/1OCC[C@@H]5C\1=C\O[C@@H](O[C@@H]4O[C@@H]([C@@H](O)[C@H](O)[C@H]4OC(=O)c3c(c2cccc(O)c2)cc(O)cc3O)CO)[C@@H]5\C=C;
Properties
Chemical formula	C29H30O13
Molar mass	586.546 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

Amarogentin is a chemical compound found in gentian (Gentiana lutea) or in Swertia chirata.[1]

Amarogentin and gentiopicrin, the bitter glycosides from gentian root

Gentian root has a long history of use as a herbal bitter in the treatment of digestive disorders and is an ingredient of many proprietary medicines. The bitter principles of gentian root are secoiridoid glycosides amarogentin and gentiopicrin. The former is one of the most bitter natural compounds known[2] and is used as a scientific basis for measuring bitterness. In humans, it activates the bitter taste receptor hTAS2R50.[3] The biphenylcarboxylic acid moiety is biosynthesized by a polyketide-type pathway, with three units of acetyl-CoA and one unit of 3-hydroxybenzoyl-CoA, this being formed from an early shikimate pathway intermediate and not via cinnamic or benzoic acid.[4]

It also shows an antileishmanial activity in animal models[5] being an inhibitor of topoisomerase I.[6]

References

Keil*, Michael; Härtle, Birgit; Guillaume, Anna; Psiorz, Manfred (2000). "Production of Amarogentin in Root Cultures of Swertia chirata". Planta Medica. 66 (5): 452–7. doi:10.1055/s-2000-8579. PMID 10909267.
Heilpflanzen:Gentiana lutea Archived 2009-09-02 at the Wayback Machine (German)
Behrens, Maik; Brockhoff, Anne; Batram, Claudia; Kuhn, Christina; Appendino, Giovanni; Meyerhof, Wolfgang (2009). "The Human Bitter Taste Receptor hTAS2R50 is Activated by the Two Natural Bitter Terpenoids Andrographolide and Amarogentin". Journal of Agricultural and Food Chemistry. 57 (21): 9860–6. doi:10.1021/jf9014334. PMID 19817411.
Wang, Chang-Zeng; Maier, Ulrich H.; Eisenreich, Wolfgang; Adam, Petra; Obersteiner, Ingrid; Keil, Michael; Bacher, Adelbert; Zenk, Meinhart H. (2001). "Unexpected Biosynthetic Precursors of Amarogentin − A Retrobiosynthetic13C NMR Study". European Journal of Organic Chemistry. 2001 (8): 1459. doi:10.1002/1099-0690(200104)2001:8<1459::AID-EJOC1459>3.0.CO;2-0.
Medda, S.; Mukhopadhyay, S; Basu, MK (1999). "Evaluation of the in-vivo activity and toxicity of amarogentin, an antileishmanial agent, in both liposomal and niosomal forms". Journal of Antimicrobial Chemotherapy. 44 (6): 791–4. doi:10.1093/jac/44.6.791. PMID 10590280.
Ray, Sutapa; Majumder, Hemanta K.; Chakravarty, Ajit K.; Mukhopadhyay, Sibabrata; Gil, Roberto R.; Cordell, Geoffrey A. (1996). "Amarogentin, a Naturally Occurring Secoiridoid Glycoside and a Newly Recognized Inhibitor of Topoisomerase I fromLeishmania donovani". Journal of Natural Products. 59 (1): 27–9. doi:10.1021/np960018g. PMID 8984149.

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[1] Keil*, Michael; Härtle, Birgit; Guillaume, Anna; Psiorz, Manfred (2000). "Production of Amarogentin in Root Cultures of Swertia chirata". Planta Medica. 66 (5): 452–7. doi:10.1055/s-2000-8579. PMID 10909267.

[2] Heilpflanzen:Gentiana lutea Archived 2009-09-02 at the Wayback Machine (German)

[3] Behrens, Maik; Brockhoff, Anne; Batram, Claudia; Kuhn, Christina; Appendino, Giovanni; Meyerhof, Wolfgang (2009). "The Human Bitter Taste Receptor hTAS2R50 is Activated by the Two Natural Bitter Terpenoids Andrographolide and Amarogentin". Journal of Agricultural and Food Chemistry. 57 (21): 9860–6. doi:10.1021/jf9014334. PMID 19817411.

[4] Wang, Chang-Zeng; Maier, Ulrich H.; Eisenreich, Wolfgang; Adam, Petra; Obersteiner, Ingrid; Keil, Michael; Bacher, Adelbert; Zenk, Meinhart H. (2001). "Unexpected Biosynthetic Precursors of Amarogentin − A Retrobiosynthetic13C NMR Study". European Journal of Organic Chemistry. 2001 (8): 1459. doi:10.1002/1099-0690(200104)2001:8<1459::AID-EJOC1459>3.0.CO;2-0.

[5] Medda, S.; Mukhopadhyay, S; Basu, MK (1999). "Evaluation of the in-vivo activity and toxicity of amarogentin, an antileishmanial agent, in both liposomal and niosomal forms". Journal of Antimicrobial Chemotherapy. 44 (6): 791–4. doi:10.1093/jac/44.6.791. PMID 10590280.

[6] Ray, Sutapa; Majumder, Hemanta K.; Chakravarty, Ajit K.; Mukhopadhyay, Sibabrata; Gil, Roberto R.; Cordell, Geoffrey A. (1996). "Amarogentin, a Naturally Occurring Secoiridoid Glycoside and a Newly Recognized Inhibitor of Topoisomerase I fromLeishmania donovani". Journal of Natural Products. 59 (1): 27–9. doi:10.1021/np960018g. PMID 8984149.